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Full text of "Practical Organic Chemistry"

AITKNDIX                                       281

Nitrosodimethylaniline is readily oxidised to nitrodimethyl-
-i niline.

It is an inlcrt-stin- fact that the nilrosnmines of the
j^tM-ondary bases undergo molecular change when acted on
xvith alcoholic hydrochloric acid. The nitroso-^roup is thereby
transferred to the para-position in the nucleus (O. Fischer),

, r-: No.c(1n,.Niicn:,

The para-nitroso derivatives of both secondary and tertiary
runiines are decomposed with caustic soda into nitrosophenol
rind alkylamine.

The formation of methylene l>luc may be explained as
follows: l>y the action of ammonium sulphide on nitroso-
tlimethylaniline, the nitroso-^mup is reduced to an amino-
j^rotip. T\\o molecules of /-aminodimethylaniline then combine
svith the elimination of ammonia to form a diphenylamine
< l<Mpivaliv<\

((. '1 1,{),X( 'i;1 1 1 ; N 1 1,    1 fi 1 1 N( \,\ I.,N(CI I,,),,

= (CMIa)aNCr,H.,.NII.CJI.,N(Cir,,)a.

The sulphur of the hydrogen sulj>hi(l(; then enters the mole-
€Mile under the oxidising influence of the ferric chloride, forming
;i thiodiphenylaiuine derivative,

II          ()            H

<('H.,).,N<;;n.,  N  <yi,,.N((:iL),,a
ii        H

II"    S    II

< >        ( >

- (Cn,,),,NCrn.,.N:CrII.,:N((''H.,),,('l.

Thiocarbanilide, Thiocarbimide, Triphenylguan-
idillO.- Whereas carbon bisulphide reacts with aromatic ami no-
compounds yi<'hlin;4 a thiocarba,nilide, with primary aliphatic
amines the reaction takes a different course and thiocarbamatcs
are produced,
cs,, i IH\,IL;NH,,^ sc,7
•                    ....       .            X-NII.G,LIB